Potassium Iodide → Butyl ether

Temperature

80 °C

A mixture of methyl 3,5-dimethoxy-4-hydroxybenzoate represented by Formula 87 (5 g, 23.56 mmol), 1-bromobutane (2.80 mL, 25.92 mmol), potassium carbonate (3.58 mg, 25.92 mmol) and potassium iodide (547.60 mg, 3.30 mmol) in DMF (50 mL) was agitated at 80° C. for 24 hours. After decreasing a temperature of the reaction mixture to room temperature, removing solids through filtration and adding ethyl acetate to the remaining filtrate, the filtrate was consecutively washed with water and a 5N-hydrochloric acid solution. After separating an organic layer and drying the same with magnesium sulfate, the solvent was removed under reduced pressure to form a concentrate mixture, which in turn, was subjected to separation and purification through column chromatography (ethyl acetate/hexane, 1:5) using silica gel (SiO2), resulting in an n-butylether compound represented by Formula 92 as a desired product (6.20 g, 94%). Analysis data of the product is provided as follows:

1. customto room temperature
2. customremoving solids
3. filtrationthrough filtration
4. additionadding ethyl acetate to the remaining filtrate
5. washthe filtrate was consecutively washed with water
6. customAfter separating an organic layer
7. dry with materialdrying the same with magnesium sulfate
8. customthe solvent was removed under reduced pressure
9. customto form a concentrate mixture, which in turn
10. customwas subjected to separation and purification through column chromatography (ethyl acetate/hexane, 1:5)

ORD record

ord-ed6bc36895454f499aaa855841f115da

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359346B2